Paradol
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MedKoo CAT#: 326793

CAS#: 27113-22-0

Description: Paradol, also known as 6-Paradol, is the active flavor constituent of the seeds of Guinea pepper (Aframomum melegueta or grains of paradise). It is also found in ginger. Paradol has been found to have antioxidant and antitumor promoting effects in a mouse model. It is used in flavors as an essential oil to give spiciness.


Chemical Structure

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Paradol
CAS# 27113-22-0

Theoretical Analysis

MedKoo Cat#: 326793
Name: Paradol
CAS#: 27113-22-0
Chemical Formula: C17H26O3
Exact Mass: 278.1882
Molecular Weight: 278.392
Elemental Analysis: C, 73.35; H, 9.41; O, 17.24

Price and Availability

Size Price Availability Quantity
200.0mg USD 450.0 2 Weeks
500.0mg USD 950.0 2 Weeks
1.0g USD 1650.0 2 Weeks
2.0g USD 2950.0 2 Weeks
5.0g USD 6650.0 2 Weeks
10.0g USD 9950.0 2 Weeks
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Synonym: 6-Paradol; Paradol

IUPAC/Chemical Name: 1-(4-Hydroxy-3-methoxyphenyl)decan-5-one

InChi Key: IKCUWBHTOKPRNS-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H26O3/c1-3-4-5-9-15(18)10-7-6-8-14-11-12-16(19)17(13-14)20-2/h11-13,19H,3-10H2,1-2H3

SMILES Code: CCCCCC(CCCCC1=CC=C(O)C(OC)=C1)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 278.392 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Setoguchi S, Watase D, Nagata-Akaho N, Haratake A, Matsunaga K, Takata J. Pharmacokinetics of Paradol Analogues Orally Administered to Rats. J Agric Food Chem. 2016 Mar 9;64(9):1932-7. doi: 10.1021/acs.jafc.5b05615. Epub 2016 Feb 24. PubMed PMID: 26868188.

2: Gaire BP, Kwon OW, Park SH, Chun KH, Kim SY, Shin DY, Choi JW. Neuroprotective effect of 6-paradol in focal cerebral ischemia involves the attenuation of neuroinflammatory responses in activated microglia. PLoS One. 2015 Mar 19;10(3):e0120203. doi: 10.1371/journal.pone.0120203. eCollection 2015. PubMed PMID: 25789481; PubMed Central PMCID: PMC4366308.

3: Haratake A, Watase D, Setoguchi S, Terada K, Matsunaga K, Takata J. Relationship between the acyl chain length of paradol analogues and their antiobesity activity following oral ingestion. J Agric Food Chem. 2014 Jul 2;62(26):6166-74. doi: 10.1021/jf500873a. Epub 2014 Jun 18. PubMed PMID: 24909840.

4: Mariadoss AV, Kathiresan S, Muthusamy R, Kathiresan S. Protective effects of [6]-paradol on histological lesions and immunohistochemical gene expression in DMBA induced hamster buccal pouch carcinogenesis. Asian Pac J Cancer Prev. 2013;14(5):3123-9. PubMed PMID: 23803090.

5: Suresh K, Manoharan S, Vijayaanand MA, Sugunadevi G. Chemopreventive and antioxidant efficacy of (6)-paradol in 7,12-dimethylbenz(a)anthracene induced hamster buccal pouch carcinogenesis. Pharmacol Rep. 2010 Nov-Dec;62(6):1178-85. PubMed PMID: 21273675.

6: Iwami M, Mahmoud FA, Shiina T, Hirayama H, Shima T, Sugita J, Shimizu Y. Extract of grains of paradise and its active principle 6-paradol trigger thermogenesis of brown adipose tissue in rats. Auton Neurosci. 2011 Apr 26;161(1-2):63-7. doi: 10.1016/j.autneu.2010.11.012. Epub 2010 Dec 23. PubMed PMID: 21185236.

7: Keum YS, Kim J, Lee KH, Park KK, Surh YJ, Lee JM, Lee SS, Yoon JH, Joo SY, Cha IH, Yook JI. Induction of apoptosis and caspase-3 activation by chemopreventive [6]-paradol and structurally related compounds in KB cells. Cancer Lett. 2002 Mar 8;177(1):41-7. PubMed PMID: 11809529.

8: Chung WY, Jung YJ, Surh YJ, Lee SS, Park KK. Antioxidative and antitumor promoting effects of [6]-paradol and its homologs. Mutat Res. 2001 Sep 20;496(1-2):199-206. PubMed PMID: 11551496.

9: Lee E, Surh YJ. Induction of apoptosis in HL-60 cells by pungent vanilloids, [6]-gingerol and [6]-paradol. Cancer Lett. 1998 Dec 25;134(2):163-8. PubMed PMID: 10025876.

Paradol

200.0mg / USD 450.0